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Resin acid refers to any of several related found in tree . Nearly all resin acids have the same basic skeleton: three fused rings having the empirical formula C19H29COOH. Resin acids occur in nature as tacky, yellowish gums consisting of several compounds. They are water-insoluble. A common resin acid is . Resin acids are used to produce soaps for diverse applications, but their use is being displaced increasingly by synthetic acids such as 2-ethylhexanoic acid or petroleum-derived .


Botanical analysis
Resin acids are and wood preservatives that are produced by epithelial cells that surround the resin ducts in trees from temperate coniferous forests. The resin acids are formed when two-carbon and three-carbon molecules couple with building units to form (volatile), (volatile), and (nonvolatile) structures.

contain numerous vertical and radial resin ducts scattered throughout the entire wood. The accumulation of resin in the and resin ducts causes a maximum concentration in the base of the older trees. Resin in the sapwood, however, is less at the base of the tree and increases with height.

In 2005, as an infestation of the Mountain pine beetle ( Dendroctonus ponderosae) and blue stain fungus devastated the Lodgepole Pine forests of northern interior , Canada, resin acid levels three to four times greater than normal were detected in infected trees, prior to death. These increased levels show that a tree uses the resins as a defense. Resins are both toxic to the beetle and the fungus and also can entomb the beetle in diterpene remains from secretions. Increasing resin production has been proposed as a way to slow the spread of the beetle in the "Red Zone" or the wildlife urban interface.


Chemical components

Biosynthesis and isolation
Resin acids originate from geranylgeranyl pyrophosphate, which is acted on (i.e., the substrate for) by copalyl diphosphate synthase. The initial conversion gives copalyl diphosphate, the progenitor of the diterpene diphosphates (nomenclature warning: pyrophosphate and diphosphate are often used interchangeably). Under enzymatic control, this pyrophosphate compound rearranges into the following diterpenes: levopimaradiene, , neoabietadiene. Traces of three other diterpenes are also generated: palustradiene, sandaracopimaradiene, and pimara-8(14),15-diene. These hydrocarbons are substrates for cytochrome P450, which introduces oxygen functionalities, i.e. converts C-H bonds to C-OH bonds and similar reactions involving oxygen in air. This conversion turn terpenes into terpenoids.

Several important resin acids can be identified in rosin, as listed below.

(2026). 9783527306732
The two classes, abietic acids and pimaric acids, are isomers with the formula C19H29CO2H.


Abietic-type acids


Pimaric-type acids


Others


Production in tall oil (chemical pulping byproduct)
The commercial manufacture of grade chemical cellulose using the kraft chemical pulping processes releases resin acids. The is conducted under strongly alkaline conditions of , , and sodium hydrosulfide. These bases neutralize resin acids, converting them to their respective sodium salts, sodium abietate, ((CH3)4C15H17COONa), sodium pimarate ((CH3)3(CH2)C15H23COONa) and so on. In this form, the sodium salts are poorly insoluble and, being of lower density than the spent pulping process liquor, float to the surface of storage vessels during the process of concentration, as a somewhat gelatinous pasty yellow fluid called kraft soap (also called resin soap).
(2026). 9783527303854
This soap is used in and cleaning and as a compound in some . It also finds use in rubber industry as an emulsifier. Often the soap is pretreated with formaldehyde and .
(2026). 9783527306732
Pine soap is refined from resin soap via tall oil by acidification, refining and resaponification.

Kraft soap can be reneutralized with to restore the acidic forms , , and related resin acid components. This refined mixture is called . Other major components include fatty acids and .

Resin acids, because of the same protectant nature they provide in the trees where they originate, also impose toxic implications on the effluent treatment facilities in pulp manufacturing plants. Furthermore, any residual resin acids that pass the treatment facilities add toxicity to the stream discharged to the receiving waters.


Variation with species and biogeoclimatic zone
The chemical composition of tall oil varies with the species of trees used in pulping, and in turn with geographical location. For example, the coastal areas of the southeastern United States have a high proportion of ( Pinus elliottii); inland areas of the same region have a preponderance of ( Pinus taeda). Slash Pine generally contains a higher concentration of resin acids than Loblolly Pine.

In general, the tall oil produced in coastal areas of the southeastern United States contains over 40% resin acids and sometimes as much as 50% or more. The fraction is usually lower than the resin acids, and unsaponifiables amount to 6-8%. Farther north in , where ( Pinus rigida)and ( Pinus echinata) are more dominant, the resin acid content decreases to as low as 30-35% with a corresponding increase in the fatty acids present.

In , where mills process ( Pinus contorta) in interior and , ( Pinus banksiana), to and Eastern White Pine ( Pinus strobus) and ( Pinus resinosa), to , resin acid levels of 25% are common with unsaponifiable contents of 12-25%. Similar variations may be found in other parts of the United States and in other countries. For example, in , and , resin acid values from ( Pinus sylvestris) may vary from 20 to 50%, fatty acids from 35 to 70%, and unsaponifiables from 6 to 30%.


Uses
are converted into by reaction with controlled amounts of or other polyhydric alcohols.

Some have , and as is used in , , and .

Resin acids are converted to .


Safety
Resin acids are very poorly soluble in water (milligrams per liter) and have low acute toxicity.


Further reading
  • discussion of early phase of this area:

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